Studies on reactions of polynitrostilbenes with sodium azide

Abstract Three polyazidonitrostilbenes were prepared via the reaction of polynitrostilbenes with sodium azide. Addition of 2 mole of this nucleophile to a solution of 3-chloro-2,2', 4,4',6,6'-hexanitrostilbene in DMF results in the substitution of azido groups for one nitro group and the chlorine in the same benzene ring. The reactions of 2,2',4,4',-6,6'-hexanitrostilbene with 2 and 4 mole of NaN3 exhibit a different reactivity and selectivity and produce symmetrically substituted azido polynitrostilbenes.